


Five Times Emma and Regina Utterly Fail at Dating

by amycarey



Category: Once Upon a Time (TV)
Genre: Dating, F/F, Fluff, Tropes
Language: English
Status: Completed
Published: 2015-06-22
Updated: 2015-06-22
Packaged: 2018-04-05 16:00:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,265
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4186011
Author URL: https://archiveofourown.org/users/amycarey/pseuds/amycarey
Summary: <blockquote class="userstuff">
              <p>Emma’s not really sure what’s happening and Henry’s perpetually embarrassed but if this IS dating it’s the worst dating Emma’s ever been involved in.</p>
            </blockquote>





	Five Times Emma and Regina Utterly Fail at Dating

**Author's Note:**

  * For [kalindasharmas](https://archiveofourown.org/users/kalindasharmas/gifts).



> For Maia on her birthday.  
> Inspired by [this](http://aimtoothpaste.tumblr.com/post/121439496328/au-scenarios-were-bad-at-dating-edition) AU post even though this ended up not being AU, so much as just wildly fluffy and tropey.

**I: One of us thinks it’s a date and the other one thinks it’s an informal job interview**

She’s not really sure what’s going on, which Regina would suggest is typical of her most of the time and she would say it in a way that would make Henry snort into his cocoa.

 

All she knows is that her annual performance review is coming up and Regina suggests that they meet at La Bella Notte for dinner that Friday. Henry sits on the end of her bed as she rifles through her wardrobe because La Bella Notte is classy, Regina Mills is classy, and Emma is not having a panic attack right about now at the thought that some snooty waiter won’t let her in the door. “Calm down, Ma,” Henry says, lying back against her quilt and crinkling the dress she has laid out across it, which at least helps cut down her wardrobe choices.

 

“I had a nightmare last night,” she says, pulling out a sheer red shirt and eyeing it. Wrinkled. Possibly she should invest in an iron. “The maître d’ refused me entry because I wasn’t wearing a tie. I failed my performance review and Regina laughed at me.”

 

“So wear a tie,” he says, all fifteen-year-old boy frustration and utter disrespect for his mother’s imminent nervous breakdown. “You know, you’re going to a lot of effort for a performance review…”

 

Emma laughs weakly. “You know your mother,” she says. “Any opportunity to mark me down…”

 

“Is that some weird sex thing?” Henry asks, looking disgusted, and Emma throws the shirt at him because it’s not like that. They’re not like that.

 

She arrives at La Bella Notte four hours later – running late to the astonishment of approximately no one – to find Regina already seated at a table in the corner. It’s secluded, which Emma appreciates because she’s not sure she wants all of Storybrooke to hear what Regina thinks of her work ethic. Again.

 

After a few minutes of small talk – Henry, how if they never hear Snow complain about swollen ankles again it’ll be too soon, the book Regina’s reading for her book club with Kathryn and Granny – Emma feels it’s time they get down to business. “I think the sheriff’s department is doing an okay job,” she says.

 

Regina’s brow furrows, just the faintest indent between her eyebrows. “Yes,” she says, almost questioning. “You’re not an entirely worthless sheriff.”

 

Emma beams at the compliment and continues. “I mean, it’s really not my fault crime rates have skyrocketed in Storybrooke over the past five years…”

 

Regina coughs. It sounds a lot like “broke the curse” but she’s smiling when she looks over at Emma, her eyes soft and sparkling and there’s something about the candlelight that makes her skin glow golden and iridescent.

 

“So,” Emma says when she realises she’s been staring just a bit too long. She coughs. “I’ve become better at turning in my paperwork as well.”

 

Regina’s lips arch into a smile. “It would hardly be possible for you to be worse,” she says. “Perhaps, though, we could talk about something else…”

 

“Oh!” she exclaims. “Like future goals and stuff? I can do that.”

 

The wrinkle in Regina’s forehead intensifies. “Emma,” she says gently. “What do you think tonight’s dinner is about?”

 

“My performance review,” Emma says and Regina’s face falls imperceptibly. “Oh God. You’re not firing me or something? This isn’t just a kind way of telling me I’m being let go? If Robin Hood becomes the new sheriff I’ll shove that bow…”

 

Regina cuts her off, hand over Emma’s, and the touch is too much that it’s hard for Emma to breath. “Of _course_ this is your performance review,” she says. “You’re just really terrible at talking yourself up.”

 

“Okay,” Emma says, and her breathing is still a bit too quick because Regina’s hand is on hers and her skin is so soft and her lips are curved in a rueful half-smile that makes Emma ache somewhere behind her breast bone. “Okay. Good.”

 

**II: I’m calling to cancel our date because I’m actually in the ER right now**

 

It’s not until her phone buzzes in her pocket that she remembers. Dr Whale is amused at the haste with which she grapples with too-tight jean pockets to fish out her phone with her non-dominant hand. “Regina,” she says, voice breathy and tight with pain.

 

“Ms Swan,” Regina says and every syllable is ice. “I know you have no sense of time but when one is invited to dinner it is polite to show up in time to eat the meal one’s host has spent hours putting together. I’ll have you know–”

 

“I’m in hospital,” Emma says, interrupting. Whale chooses that moment to yank at her arm as he layers the plaster. “Ah, fuck!” She looks over at him, glaring, and he shrugs an apology.

 

There is silence down the phone, before she hears the dial tone. “Well,” Emma says to Whale. “That went spectacularly.”

 

The next thing she knows, however, Regina bursts into the room in a whirl of angry energy. “Your _incompetent_ nurses wouldn’t tell me where Ms Swan was,” she tells Whale who looks as though he’s trying not to laugh. “I suggest you remind them who runs this town. I can make their lives very miserable. I can make _everyone’s_ lives miserable.”

 

“Okay,” Whale says, drawing out the last syllable. “We’ll just let the plaster set, Emma. I’ll let you and the missus have some time alone.”

 

“We’re not…” Emma starts but Whale has left the room and all of Regina’s intensity is now focused on her. She’s so tightly wound, nostrils flaring and the vein in her forehead throbbing as she struggles to maintain control.

 

“What happened?” Regina asks after some deep breathing and, Emma suspects, counting to ten.

 

“I don’t want to talk about it,” Emma mumbles, before adding, “you didn’t have to come down here.”

 

“I know,” Regina says, and she sighs. She’s still pacing frantically though, heels clipping sharply against linoleum, the sound reverberating through Emma’s head. “You _idiot._ ”

 

“I’m fine,” Emma says. “Where’s Henry?”

 

“At Nick’s house,” Regina says, distracted. “He has a sleepover.”

 

Her head pounds. It’s probably a concussion – not the fact that Henry wasn’t going to be present at what Emma had assumed was a family dinner – even though Whale has determined that she doesn’t have a concussion, that the scrape on her forehead is superficial. “Why would he be at Nick’s?”

 

“Honestly!” Regina huffs. Whale re-enters.

 

“Do you have somewhere to stay tonight, Sheriff?” he asks, handing her a prescription for pain killers. The good pain killers.

 

“She’ll stay with me,” Regina says in a tone that brooks no opposition. Nonetheless, Emma tries.

 

“I can call my parents,” she says. She’s not entirely sure why they weren’t contacted earlier, though she’s grateful. Snow would fuss. Regina rolls her eyes and ignores her.

 

As Whale explains to Regina about Emma’s arm, she finally gets a chance to look at her – the still life rather than the Road Runner animation. She’s dressed beautifully, but then she always is, and her hair is coiled back at the nape of her neck, baring a whole new playground of exquisite skin over which Emma can fantasise. She leans back against the hospital bed, closing her eyes, and refuses to open them until Regina hoists her upright.

 

Regina has apparently made it here by magic, so after filling her script at the pharmacy, Regina transports them to the Mifflin Street house by magic, forcing Emma onto the couch and handing her a bottle of water and her pain killers. “Explain,” she says, standing over her, arms crossed. She’s five feet and four inches of intimidation in stockinged feet and Emma should not be, like, turned on by this.

 

“I said I didn’t want to talk about it,” she says. The pain meds are already going to her head, not helped by the drugs Whale gave her at the hospital earlier to dull the pain of her fractured arm.

 

“I can always ask around,” Regina says. “Leroy knows _everything_. We’re buddies now.”

 

“Fine,” Emma says with a groan. “IfelloffthetrollbridgechasingPongo.”

 

The drawn, anxious look on Regina’s face melts away as she deciphers what Emma has spat out and she laughs, the sound deep and tugging at something in the very core of Emma. “Idiot,” she says.

 

“You’re supposed to be nice to the injured,” Emma replies, pouting.

 

“Oh please,” Regina says. “I’ve been more than nice. Look at those fluffed cushions behind you.”

 

But she heats up dinner – the meat a little dry (“which is entirely your fault, Swan, I’ll have you know”) – and cuts up all of Emma’s food into bite-sized pieces so she doesn’t have to worry about using a knife and, when Emma starts to yawn, she helps her upstairs, handing her a loose nightgown that she’ll be able to pull on without her cast getting in the way. She returns when Emma has snuggled under the covers of the duvet in the guest bedroom.

 

Emma’s voice is slurred with exhaustion. “Thanks, Regina,” she murmurs, her silhouette all Emma can see in the dim light and through half-closed eyes.

 

“Good night, Emma,” Regina says and closes the door, enveloping Emma in darkness.

 

**II: I can’t tell whether this is a date because you asked to see a movie but I’m still not sure you’re queer**

 

Emma’s really not sure what’s going on at this point and so she turns to Henry when he’s back with her the following weekend. “So, you were at Nick’s the other night. Did your mom invite me over for dinner alone to poison me or…”

 

Henry doesn’t even look up, intent on his reading. “I’m not even talking about this whole thing you guys have happening. It’s too weird for words.”

 

“But Henry,” Emma says, leaning forward so that her face is very close to his. “Was it a date?”

 

“Shut up,” Henry says, grabbing his book and stomping out of the living room.

 

“Just tell me,” she yells after him. “Don’t you want your moms to be happy?”

 

“I hate you,” he calls back, slamming the door to his bedroom.

 

Emma scowls after him. Her phone chimes. “Hey, Regina,” she says, answering.

 

“There’s a film on tonight that I would like to see,” she says. “Come with me tonight.”

 

“Since you asked so nicely,” Emma says, holding the phone between her shoulder and ear so she can rummage one-handed through the fridge.

 

“I’ll meet you there at seven,” Regina says and hangs up, at which point Emma realises she doesn’t even know what film she’s agreed to see. She can’t call back though and it’s not like she’s going to decline even it is some Cold War documentary so she makes a sandwich with leftover salami and a whole lot of pickles and takes it to Henry’s room.

 

“No,” he says. “Go away.” However, he takes the sandwich and bites into it (and her kid has terrible tastes in food to the point where she sometimes wonders if he’s having pregnancy cravings) so Emma settles down on the end of his bed, clutching one of the cushions Snow embroidered for him to her chest.

 

“Henry,” she says. “Buddy. My only son. Light of my life. Fruit of my loins. Just a couple of quick questions.”

 

Henry looks like he might puke, which, well, she could have told him that pickles and salami were a stupid combination. “No.”

 

“What movie am I going to with your mom tonight?”

 

He glares at her. “How would I know? It’s my week with you. Is that all?”

 

“Second question,” Emma says. “Is your mom bisexual?”

 

She narrowly misses the bread and meat as it flies across the bed at her. It lands against the wall instead and Henry’s lucky she’s the cool mom because Regina would be super pissed that the pickle was going to stain the wallpaper. Not Emma though. Mostly because she’s laughing too hard to speak.

 

She doesn’t want to dress up too much because what if this isn’t a date? It probably isn’t a date. As far as Emma knows, Regina’s only into men. As far as Emma knows, Regina isn’t into her even if she is into women in general. Still, she finds herself wearing a nicer version of her usual fare and standing outside the cinema ten minutes before time. Take that, Regina.

 

When Regina arrives, she smiles swiftly and brandishes their tickets. “I bought them online.”

 

“How much do I owe you?” Emma asks.

 

“Get us some popcorn,” Regina says, waving away Emma’s wallet. So, she’s paid for her tickets. Check one for this being a date. Emma buys them a large carton of popcorn and they sit side-by-side in the cinema, Regina’s hair tickling Emma’s shoulder and, when they reach for the popcorn at the same time, Emma’s hand brushes her and she’s glad it’s dark because her face feels like it’s on fire.

 

The movie is not a romance, which depresses her because that would have been the second check mark for this being a date. However, it’s also the action movie Emma’s been trying to convince Henry they should go to together for two weeks. He keeps refusing because apparently it’s not cool to go to the movies with your mother, even though she knows he and Regina go on movie dates sometimes. She was really hurt when she discovered this until she found out they go to European art-house films together because Henry is the surest case of nurture over nature that she’s ever encountered, the pretentious little shit.

 

She didn’t realise Regina was into action movies. If she’d known she’d have dragged her along to the movies a lot sooner.

 

She’s contemplating the ‘yawn and stretch’ manoeuvre when she looks in front of her and sees Will Scarlet. He leers back at her and mouths “cop a feel” and Emma leaps away from Regina, upending popcorn into her lap.

 

Regina looks over. “Is the bitty sheriff a bit scared?” she whispers, pronouncing her ‘r’s as ‘w’s.

 

“Shut up,” Emma hisses, brushing greasy popcorn off her best jeans. The potential for a date-like atmosphere is ruined and it’s entirely possible Emma will murder Will Scarlet when she has to haul his drunk ass in because of a drunk and disorderly complaint.

 

**IV: You bought me at a charity auction and you’re probably a serial killer**

 

“I can’t believe you’re making me do this,” Emma says, pulling faces at herself in the mirror as she lets Snow make the final adjustments on her gown. Her arm is out of plaster now and she wonders whether she’s imagining her recently healed arm to be smaller than the other arm.

 

Snow laughs, zipping up the dress and hugging her from behind, her protruding belly pressing against Emma’s back. “It’s for a good cause,” she says.

 

“It’s for the nuns,” Emma responds. “They’re dicks. They’re not even nuns anymore. They just wear the costume. It’s utterly fraudulent.” She’d heard Regina say this the other week and liked the way it sounded.

 

“Emma!” Snow exclaims, scandalised. “You cannot call the fairies ‘dicks’!”

 

“Isn’t this whole auctioning people off for charity thing a bit seedy anyway?” Emma asks, attempting to adjust the bodice of her dress. It’s too tight, constricting her boobs, though Snow keeps telling her it’s just how dresses were back in the Enchanted Forest.

 

(“Regina used to wear these corsets,” she’d said with a misty look in her eyes. “Her décolletage was really quite magnificent.”

 

“Gross, Mom,” Emma had said mildly.)

 

“It’s a bit of fun, darling,” Snow says, tucking an errant curl back behind Emma’s ear. “You look beautiful.”

 

David is the master of ceremonies and he grins at her when Emma approaches the edge of the stage to get auctioned off rather like one might approach the firing squad. “Up next we have our sheriff and saviour,” he says. “She’s beauty and she’s grace…”

 

She zones out at this point, peering out at the crowd. She thinks she sees Regina, dressed in black and nursing a glass of red wine and she remembers Snow’s outrage when Regina had refused to take part.  “Honestly!” Snow had said. “She threatened to set me on fire.”

 

“So it was a new and special moment in your relationship,” Emma had replied. Snow hadn’t spoken to her for an hour after that.

 

“And we’ll start the bidding at one hundred.”

 

She sighs. Archie starts off the bidding and then Hook gets in on it and Emma’s not entirely sure where he’s got the money from but she bets he’s been _saving_ and this has to be Snow’s idea (“but you were such a lovely couple,” she’d said after they broke up _two years ago_ ). Why didn’t she just give Henry access to her entire bank account and blackmail him into bidding everything on her?

 

“Do I have any further offers on five hundred?” David asks. Hook is leering and she remembers that he told her, when they broke up, that he’d never give up on her and why had she dated a guy who didn’t understand ‘no means no’ in the first place? Jesus.

 

“Nine hundred and thirty eight dollars and, oh, seventy-three cents,” comes a ringing voice. Emma looks over at Regina who is smirking over at Hook whose expression has darkened, mutinous. She’s willing to bet that it’s a penny exactly over the amount of money in his bank account.

 

“And the charity date with the saviour is sold to the evil queen,” David says and adds more quietly, “nice bit of symmetry there.”

 

Emma is handed a hamper (because the date is apparently immediately after auction (wouldn’t want to women to change their minds and dodge calls) and escorted off stage and handed over to Regina. She places a proprietary hand on her arm and Emma barely has time to mutter a fervent “thank you” before they’re whirled up in a cloud of purple smoke.

 

They end up at Emma’s apartment. “Seriously,” Emma says, still clutching Regina’s arm and she’s pretending it’s for balance. “Thank you so much.”

 

“Anything to humiliate Hook,” Regina says, though her eyes glint with supressed merriment. One heeled foot kicks out at the X-box remote lying on the floor of the living room. “Quite the romantic set-up you have here.”

 

“I didn’t realise I’d be coming to my place with my date,” Emma says. “It’s very forward of you.”

 

Regina’s tongue flicks out, darting against plum lipstick. “Quite,” she says. “If this were a date, of course…” Before Emma has the chance to feel unduly disappointed, Regina adds, “I’m not in the habit of purchasing my dates.”

 

“There’s a first time for everything,” Emma says and opens the hamper. “Ooh, pie!”

 

“For dessert,” Regina says, slapping her hands away.

 

“Fine,” Emma sighs. “I should probably lose this ridiculous dress though. Unzip me?”

 

Regina moves behind her, her breath warm on Emma’s neck and she feels the tips of her fingers dance across her skin at the point where bodice meets back. “Why did Snow dress you in pastels?” she asks. “You should only wear bold colours.”

 

Emma breathes in a sharp, shuddering breath. “I don’t know,” she says. She hears the snick of the zip being pulled down. Too late, she remembers the tight bodice of the dress meant going without a bra, feels Regina’s knuckles brush against naked skin, trailing the nubs of her spine, and she shivers.

 

“Oh my God,” Henry says, opening the apartment door. “Ma!”

 

“Why is only one person being blamed for this?” Emma asks, hand clutching at the satin of the dress.

 

“Go and find your birth mother, Henry,” he says, mimicking himself at ten as he storms past her towards his bedroom. “She’ll be really cool and not embarrassing _at all_.”

 

“Put a bra on, Emma,” Regina says, hurrying after Henry, and so, deflated, Emma retreats to her bedroom where she pulls on sweatpants and a loose sweatshirt (no bra, because Regina can’t tell her what to do).

 

Henry is coaxed out of his room by pie and the promise of a glass – just one – of champagne. It’s a pleasant evening with her son and his mother, though, in bed alone at the end of the night and sleep eluding her, Emma can admit to herself that it’s not how she wished for her evening to end.

 

**V: We had sex at the office party but we’re both workaholics so we don’t normally date**

 

A couple of weeks after the charity auction she’s having lunch with Regina in her office, vaguely discussing town business, when the stupidest conversation of all time happens. “It’s really unfair that Storybrooke doesn’t do staff Christmas parties,” she says and takes an indelicate bite of grilled cheese.

 

Regina scowls and steals a fry. “Explain,” she says. “Please.”

 

“I just feel like we’re missing out,” she says. “Getting drunk with workmates on the company dime and camaraderie and terrible catering and people having sex on the photocopier.”

 

“Your only colleague is your father,” Regina says. “I think I was right in trying to keep Henry away from you all these years.”

 

“Hah hah,” Emma says. “Just, don’t you think we’re missing out?”

 

“I do not,” Regina says. “Now, about your budget for next year.”

 

The next weeks past in a blur of enchanted mistletoe and an infestation of pixies coming through a portal from the Enchanted Forest – nothing major, but it keeps the sheriff’s department busy. It’s the week before Christmas when she trudges into the station after hours, having sent David home for the night. She’s exhausted and cross and she fell into snow drifts three times on the way here and she hasn’t seen Regina in almost ten days, and she’s pretty sure she’s addicted to her given the amount of questions she has for Henry when he’s staying with her.

 

“Oh my God, Ma,” he’d said last night, the words exploding out of him like the baking soda volcano he’d made for the seventh grade science fair. “Just ask her out already.”

 

“I, what?” Emma had asked, blinking. “That’s so not the point, kid.”

 

So now it’s a week before Christmas and she _wants_ so desperately that when she opens the door to the sheriff’s station and finds it a) decorated in festive cheer b) playing ‘Snoopy’s Christmas’ and c) occupied by Regina Mills, dressed in red and wearing a sprig of holly in her hair, she’s pretty sure she’s having some sort of fever dream. “Welcome to the work Christmas party,” Regina says, sauntering forward and handing Emma a glass of champagne. Emma takes a sip. Cheap and nasty sparkling wine. Perfect for Emma’s imagined office Christmas function.

 

“What’s happening?” Emma asks.  

 

“You wanted a Christmas party,” Regina says. “The town wants employee satisfaction.”

 

“The town?” She downs the rest of the wine. There are Christmas lights wreathing the walls, glinting red and green and gold, and there’s even a tree set up in the corner by filing cabinets.

 

Regina nods. “The town thinks it has a pretty great sheriff,” she says. “The town wouldn’t want to lose its sheriff to a big city.” She’s standing awfully close, voice throaty and whispering in Emma’s ear and Emma can’t breathe.

 

“Oh my God,” she hisses.

 

“The town also thinks you have a cute butt,” Regina says.

 

“Did the town pre-game this party?” Emma asks and Regina shakes her head. “Good,” she says and she bridges the gap between them and kisses Regina.

 

Regina’s mouth is soft and pliant against hers and Emma can’t quite believe that she’s kissing her, that this isn’t some joke or dream, that Henry won’t walk in at any moment to spoil the moment. She bites Regina’s lower lip and the whimper that escapes her makes her shiver and she drags her fingers through Regina’s hair, dislodging the holly. It falls to the floor.

 

“You mentioned something about a photocopier?” Regina whispers in Emma’s ear.

 

“You are my favourite person in the universe,” Emma says fervently.

 

She has no cause to regret these words, not when Regina’s mouth is hot against her neck, not when her fingers wind their way down, unzipping Emma’s jeans, not when she’s hoisting Emma up onto the photocopier. She has no cause to regret anything when Regina’s two – and then three – fingers deep, thumb circling her clit, teeth grazing her clavicle, and Emma’s breath stutters and her eyelids flutter and she _moans_.

 

No regrets whatsoever.

 

“So,” she asks, sitting in her desk chair with Regina on her lap, fingers drawing patterns on Regina’s thigh. Regina has Emma’s coat wrapped around her shoulders and her head is nuzzled against Emma’s neck. “What does this mean?”

 

“Well, we have had at least three dates by this stage,” Regina says. “Four if you count the hospital incident. It was about time you put out.”

 

“We have not had three dates,” Emma says, outraged. “I would know if we’d been on three dates.”

 

“You’re unbearably dense,” Regina says, though her smile is fond.

 

“You never _asked_ me on any of these so called dates,” Emma replies. “I can’t read minds.”

 

“I should have thought it was perfectly obvious,” Regina says but colour stains her skin.

 

“I’ve been _agonising_ ,” Emma says. “I had no idea.”

 

“Oh for God’s sake,” Regina says, shifting. She looks directly into Emma’s eyes. “Emma Swan, will you go on a date with me?”

 

“I thought you’d never ask,” Emma says.

**Author's Note:**

> The 'town' stuff was inspired by 'Parks and Rec' and fit in delightfully with mockery from yesterday.


End file.
